Arsanilate salts of hydroxyquinolines



Patented Apr. 13, 1954 UNITED STATES PKTENT' OFFICE ARSANILATE SALTS FHYDRO- QUINO LINES Geza S. Delmar, Montreal, Quebec, Canada No Drawing.Application January 9,1952,

epial No. 265,721

edltims. (o1. geesm Remnant" The treatment of amebiasis r. trichomonasvaginitis infections h sbeendone withbismutll salts, arsenicals and.fiahydiioii ll irlqline, or its derivatives. f r example, the nhlorendeer the diiodo derivatives of 8'-hydroxyquinoline. Recently theseinfections have been treated with salts which are-made'up of bismuttiandarsenicals, for example, Ele'ismuth' glycolylarsanilate. Since mostof these compounds are relatiyely toxic, and that theymustheadmintstered in fairly large doses in ordertobe efiective,.iorexample, 0.5 g. daily in the ease of carb'arsone(p-carbamylaniinophenylarsonicacid) there is always .a danger ofundesirable side reactions,

It is therefore seenthat'litwls de r ble tom tain a compound which willbe effectiv against protoz oan infections in relatively small dosagesand which Will reduce the normally occurring side reactions to aminimum.

K APPLICANTS DEVELOPMENT In accordance with the present invention it hasbeen found that salts corresponding to the general formula:

NHR

N/ I HO-As- OH OH 1 2 v The 8 hydroxyqninoline. halogenated derivativeswhich may be used are preferably the chloroiodohydroxyguinoline or thediiodo-hydroxyquinoline.

he ars n l ea id derivat v s use o respond to the general formula;

wherein R ishydrogen, acyl, hydroxyacyl, or -CONH2 and R1 is hydrogen.

The reaction'is' carried out in the presence of a solvent for thereactants, for example, methanelt thanol. or a tone EXAMPLES The;reparationoftheproducts of the Present invention wiiI 'b'emore fullyunderstood by referring to the following examples, but it is to beunderstood that they are not to be taken as limitative of the inventionsince equivalent procedures and variations in reactants may be usedwithout departing from the spirit of the invention.

Example 1 14.5 gm. of 8-hydroxyquinoline are reacted in the presence ofmethanol with 27.5 gm. of glycolylarsanilic acid. The salt ofB-hydroxyquinoline glycolylarsanilate results, which has a melting pointof 152-162 C. under decomposition.

Instead of methanol, also ethanol, acetone or any other suitable solventmay be used in the reaction.

Example 2 Instead of B-hydroxyquinoline, there may be used in the abovereaction, 30.5 gm. of the chloroiodo derivative (Vioform) and theglycolylarsanilate of chloro-iodohydroxyquinoline will result with amelting point of 1'77-l78 C.

Example 3 Taking in the above example, 39.7 gm. diiodohydroxyquinolineinstead of B-hydroxyquinoline there is obtained diiodoquiolineglycolylar- NHR N on 110- -cH wherein X is a radical selected from thegroup 4 gen, comprising, reacting in the presence of a solvent an8-hydroxyquinoline compound of the formula:

I N OH with an arsanilic compound of the general formula:

' to obtainthe desired s-hydroxyquinoline salts.

consisting of halogen and hydrogen, R is a radical selected from thegroup consisting of hydrogen, acyl, hydroxyacyl, and CONH2 and R1 ishydrogen.

2. As a new compound, the glycolylarsanilate ofchloro-iodohydroxyquinoline.

3. As a new compound, the of diiodohydroxyquinoline.

4. As a new compound, the glycolylarsanilate of S-hydroxyquinoline.

5. A method for preparing the 8-hydroxy-.

quinoline salts of the general formula:

wherein X is a radical selecte'd from the group consisting of halogenandhydrogen, R is a radical selected from the group consisting ofhydrogen, acyl, hydroxya'cyl, and -CONHz and R1 ishydroglycolyl'arsanilate 6. A method for preparing glycolylarsanilate ofchloro-iodohydroxyquinoline, comprising reacting in the presence of asolvent glycolylarsanilic acid withchloro-iodohydroxyquiholine to obtainthe desired 8-hydroxyquinoline salts.

7. A method for preparing the glycolylarsanilate ofdiiodohydroxyquinoline, comprising reacting in the presence of a solventdiiodohydroxyquinoline with glycolylarsanilic acid to obtain the desired8-hydroxyquinoline salts.

8. A method for preparing the glycolylar- 'sanilate of8-hydroxyquinoline, comprising re- ;acting in the presence of a solventS-hydroxy- 'quinoline with glycolylarsanilic acid to obtain thedesired8-hydroxyquinoline salts.

' References Cited in the file of this patent UNITED STATES PATENTS"Number Name Date f 2,039,577 Renda et al May 5, 1936 2,557,353 1'Kartsonis et al June 19, 1951 FOREIGN PATENTS Number- Country Date"419,632 Great Britain NOV. 13, 1934

1. AS NEW COMPOUNDS, 8-HYDROXYQUINOLINE SALTS OF THE GENERAL FORMULA: